Sodium Hydroxide → HCID 178517490, compound

To a solution of 2-amino-4-(2-pyridyl)pyrimidine (10.10 g, 58.66 mmol) in 5% aqueous sulfuric acid (200 mL) was added sodium nitrate (20.24 g, 293.3 mmol) portionwise over 10 min. The solution was stirred at room temperature for 2 h and was then adjusted to pH 10 by addition of 6N aq. NaOH. The resulting mixture was then extracted with 30% i-PrOH in CHCl3 (10×300 mL), and the combined organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was triturated with hexanes and collected by vacuum filtration to afford 6.89 g of 4-(2-pyridyl)pyrimid-2-one (68%) as a beige solid. A mixture of 4-(2-pyridyl)pyrimid-2-one (6.89 g, 39.8 mmol) in phosphorus oxychloride (30 mL) was heated at 110° C. for 90 min in a sealed tube. The dark brown solution was then cooled to room temperature and poured over cracked ice and water (500 mL). The mixture was vigorously stirred at 0° C. for 1 h, and was then adjusted to pH 14 with 6 N aq NaOH. The mixture was extracted with CH2Cl2 (2×300 mL), and the combined organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. To a solution of the residue in CH2Cl2 (10 mL) and MeOH (30 mL) was added hydrazine monohydrate (7.0 mL, 144.2 mmol), and the solution was stirred for 16 h at which time a white precipitate was observed. This solid was collected by vacuum filtration, washed with water, and dried in vacuo to provide 2.20 g of the title compound (30%) as an off-white solid. MH+188.

1. extractionThe resulting mixture was then extracted with 30% i-PrOH in CHCl3 (10×300 mL)
2. dry with materialthe combined organic phase was dried over anhydrous MgSO4
3. concentrationconcentrated in vacuo
4. customThe residue was triturated with hexanes
5. filtrationcollected by vacuum filtration

ORD record

ord-3a5563953e0a43a9bd1424f33d305e87

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919528B2